1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 53667316, compound

HRID 322805Notes

Reaction equation

HRID 322805 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[CH2:13]=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:13]([O:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11])[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 81251-Octene

Product 1

HCID 53667316HCID 53667316, compoundYield 83%

Conditions

Temperature
100 °C

Procedure

A mixture of 20.0 g (0.12 mol) of 1-oxyl-4-hydroxy-2,2,6,6-tetramethylpiperidine and 164.0 g (1.04 mol) of 1-octene is heated under a nitrogen atmosphere at 100° C. for 24 hours, and then for an additional 24 hours at 115° C. The reaction mixture is filtered to remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine, and the filtrate is washed with 10% (w/v) ascorbic acid (2×50 mL) and distilled water (2×50 mL). The organic phase is dried over anhydrous magnesium sulfate and the volatiles removed in vacuo. The residue is chromatographed to give 14.4 g (83% yield) of the title compound as an amber oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine
  3. washthe filtrate is washed with 10% (w/v) ascorbic acid (2×50 mL)
  4. distillationdistilled water (2×50 mL)
  5. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  6. customthe volatiles removed in vacuo
  7. customThe residue is chromatographed

Sources & evidence

ORD record
ord-062b5399541f4783866608e5d2080231
Source dataset
uspto-grants-2001_04
Patent number
US06211378B1

Reaction notes

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